Nota bene: All products in this article are independently selected and vetted by InsideHook editors. If you buy something, we may earn an affiliate commission.
To all those folks who doubted me when I called that the Gap was on a comeback tour: apology accepted. The mall brand has been an American institution for decades. Even having fallen out of favor for a few years, it was only a matter of time before the retail giant reestablished its stranglehold on easy-access apparel.
To the Gap’s credit, they worked hard to recommit themselves to a younger, more on-trend brand of cool, enlisting the help of both behind-the-scenes creatives and big-name talent. (Their latest campaign, a fall denim edit, spotlighted in-demand stars in the form of Obsession actress Inde Navarrette and psyop pop sensation Malcolm Todd.) And, for the most part, it’s worked: The latest collection, a mishmash of modern basics and ’90s-inspired staples, offers designs aligned with what consumers want nowadays: affordable, retro-leaning styles in a variety of wider ‘fits.
It’s worth mentioning that, the Gap’s discount-forward proclivities, many of these new styles are already on sale: below, I’ve highlighted some of my favorites from the collection, all of which are on sale. Shop them below, or check out more apparel here.
Gap Sale Guide
- The Cropped Tee: Gap Heavyweight Crop T-Shirt,
$40$31 - The Mandatory Military Jacket: Gap Oversized Field Jacket,
$118 $70 - The ’90s Jeans: Gap Baggy Jeans,
$80$31 - The Relaxed Knit: Gap Relaxed Shaker Sweater,
$60$47 - The Straight-Cut Shirt: Gap Relaxed Straight-Hem Flannel Shirt,
$70$48 - More Deals
Gap Heavyweight Crop T-Shirt
For those of us without an eight-pack (read: everyone), it’s easy to be intimidated by a cropped shirt. Fear not: Gap’s heavyweight design is more of a hits-right-at-the-waist fit, with just enough coverage to let your slutty little tee flag fly without completely forgoing modesty.
Gap Oversized Field Jacket
You heard it here first: military-inspired outwear — particularly field coats like this one — are about to be everywhere.
Gap Baggy Jeans
The hero item of Gap’s fall campaign, the Baggy Jean comes in about a dozen washes and, given its excessive size, should work in establishing a serious rock star vibe for anyone (not just Malcolm Todd types).
Gap Relaxed Shaker Sweater
The cardinal rule of early fall fashion: the coolest thing you can wear is a ribbed sweater and jeans.

